Wig Stories

6,038 results
Orientation
Length
Source
Infinite Scroll

Was He Becoming A Cross Dresser Ch. 05

by Alpha2Bravo on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 5 THE WIG WAS PERFECT After nearly killed myself with my eyes rolled back in my head doing 85 miles an hour. I snapped I was driving and started to slow down to the speed limit and get control of myself, my cock and my pants. It was a lot easier to push my pants down then to pull them up while driving but I got it done. Once I had relaxed a little...

Stop on the Road Trip

by borntoplease on Sep 14, 2017
Group Sex

It was a beautiful day in late spring and my husband and I were going on a trip out of town for the weekend. We have been together for 17 years and while things have always been good in our sexual relationship, we have from time to time tried to spice things up. Before this trip I thought I would try something that I never had before. I bought a longhaired...

Mommy Adriana and the Video Booth

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, I never imagined to get so far but funnily the more I write the more ideas I get. I hope you still enjoy the ride. * I closed my eyes. Not wanting to see people staring at the bound and gagged bundle which I had no doubt they were, especially when we stopped at red lights. In fact I didn't see where we were going. The only thing I...

A Virtual Change in Behavior Ch. 02

by AimeeDaze on Oct 9, 2017
Transsexuals & Crossdressers

When I came back around I could see light. It took my eyes times to focus, and when they did I realised I was looking up at Jeff's bedroom ceiling. I was still groggy as hell, like I hadn't slept in days, even although I knew I had. I tried to move again, but my arms were still bound. I could move my legs though and I stretched as best I could. I felt the si...

A Long Distance Affair Ch. 02

by IrishRose1215 on Sep 12, 2017
Erotic Couplings

David and I kept up the e-mails after he went home, and one day while I was reading his words I thought to myself, "I'd love to see him again." I wrote my response and then began to daydream about seeing him. I decided that I would go to Australia, without a word to him that I was coming. I would surprise him, this time I wanted to play a game. I had loved m...

Wife Converts Husband Ch. 02

by bisexual_slut on Sep 25, 2017
Transsexuals & Crossdressers

This story is totally fictional and any resemblance to anyone is purely coincidental. We end up going to a big lingerie shop and buy several pairs of g-strings, booty shorts, bra's, corsets, suspender belts and stockings of all colours and styles, which Shelley thought would best suit me and a pair of breast forms to give me real looking breasts. We then we...

Halloween, Aka: Tour De Force

by thechangedone on Sep 14, 2017
Transsexuals & Crossdressers

My name is Paul Nether. I am a 25-year-old Caucasian man. I am currently employed as an English language teacher. Not my dream job by any means, but it will have to do. I wish I could just open a portal to a better world, but this is not going to happen anytime soon. Also, forgive me for not adhering to the, "show, don't tell" rule. I hope you can understa...

The Bet

by latexcd69 on Sep 12, 2017
Transsexuals & Crossdressers

My friend Cristina and I were just sitting around watching porn. It's something we do for fun now and then. Believe it or not, it has never led to anything. A scene came on where a guy was put in a wig and satin nightgown and fucked by a beautiful blond dominatrix with a strap on. We laughed at what an ugly girl he made and somehow it came up that I had a gi...

Bobby's Weekend

by angelle420 on Sep 16, 2017
Transsexuals & Crossdressers

Bobby ran up the stairs as fast as he could. It was four o'clock and his stepfather would be home in two hours. He had three bags in his hand from his shopping trip that he threw on the bed as soon as he got into his bedroom. Quickly, he turned back up the hall and towards the bathroom to get in the shower. He turned on the water stripped, and got in. He the...

High Rise Antics

by Arrtemis on Oct 5, 2020
Erotic Couplings

Hello my name is Peter, I am a security officer at a major international bank in Canary Wharf, London. One of my responsibilities is to review the files from the bank's CCTV cameras. Each camera has a sound/motion sensor, only recording when it detects activity. Recently one of the six, in the first class lounge, recorded a very interesting incident. A well...